Methanol → 5-(5-(3-chloropropylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazole

HRID 1661064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1661064
[CH3:1][C:2]1[S:3][C:4]([C:8]2[N:9]([CH3:14])[C:10]([SH:13])=[N:11][N:12]=2)=[C:5]([CH3:7])[N:6]=1.CO.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27]>C(OCC)(=O)C.CC(C)=O>[Cl:27][CH2:26][CH2:25][CH2:24][S:13][C:10]1[N:9]([CH3:14])[C:8]([C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])=[N:12][N:11]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178432727HCID 178432727, Verbindung

Produkt 1

HCID 446278985-(5-(3-chloropropylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazoleAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

5-(2,4-dimethylthiazol-5-yl)-4-methyl-4H-1,2,4-triazole-3-thiol (Prep27, 5 g, 22 mmol) was added to a mixture of methanol (15 ml) and acetone (35 ml), followed by K2CO3 (5 g, 36 mmol) and 1-bromo-3-chloropropane (35 ml, 36 mmol). The suspension was stirred at 22° C. for 24 h. The volume of solvent was reduced, then ethyl acetate (63 ml) was added and the organic layer was washed with water, the EA was removed under vacuum and the crude purified by FC (EA/MeOH 15:1) to afford 2.5 g of pure product (y=37%).

Aufarbeitung

  1. washthe organic layer was washed with water
  2. customthe EA was removed under vacuum
  3. customthe crude purified by FC (EA/MeOH 15:1)

Quellen und Nachweise

ORD-Eintrag
ord-10eff361006c4b3ea2b609b2d6ddd6a3
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030322B2

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